The Fashion Goal
You don't want to over-glamorize your look to the point that it is trashy, so avoid those shiny stiletto, thigh-high boots. The main goal is to offer length and slenderize your silhouette. Over the knee boots should work to create a taller, leaner you and never create a look that appears stumpy or broken up. If you are wearing tights with the boots, match the color or wear skinny pants that compliment the boot color and are tucked inside the boots to offer an appearance of an extended leg line.
The main point is to not create too many lines that break up the outfit and can leave you looking frumpy. Wear clothing that contrasts well with the boots and creates a long and slender leg line. Below are some options for what to wear with your over the knee boots.
Skinny jeans are a great option for wearing your over the knee boots and looking amazing. When you find the perfect pair of jeans that fit you just right, add the long boots to them and create a high fashion look that is ready for any runway. If you pair the jeans and boots with a jacket or blazer that comes down below the buttocks, you can create a sophisticated and stylish look. If you want something a bit more casual, try an oversized sweater that is long enough to come down past the buttocks of the jeans. Make sure the sweater is not so much baggy as it is long; you don't want to appear lopsided in size from top to bottom.
If you want to wear the long boots with short skirts, rule of thumb is to always wear tights. Don't let your naked leg show; use tights that closely match the color of the boot and wear a skirt that contrasts the color nicely. You can create an illusion of longer legs by wearing the same color tights and boots. The short skirt works to create a line that the eye is drawn to, and by adding a layered look on top, you create an even more stylish look. Try a sexy silk green blouse with a brown and black blazer that fits tightly around the waist and hangs below the buttocks with a black skirt, brown tights and brown over the knee boots.
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